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1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C 8 H 8. It is also known as [8] annulene . This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature.
Cyclooctatetraene is another example of a molecule which is not antiaromatic, even though it might initially appear to be so. Cyclooctatetraene assumes a tub (i.e., boat-like) conformation. As it is not planar, even though it has 4n π-electrons, these electrons are not delocalized and conjugated. The molecule is therefore non-aromatic.
Aromaticity is found in ions as well: the cyclopropenyl cation (2e system), the cyclopentadienyl anion (6e system), the tropylium ion (6e), and the cyclooctatetraene dianion (10e). Aromatic properties have been attributed to non-benzenoid compounds such as tropone. Aromatic properties are tested to the limit in a class of compounds called ...
In chemistry, the cyclooctatetraenide anion or cyclooctatetraenide, more precisely cyclooctatetraenediide, is an aromatic species with a formula of [C 8 H 8] 2− and abbreviated as COT 2−. It is the dianion of cyclooctatetraene. Salts of the cyclooctatetraenide anion can be stable, e.g., Dipotassium cyclooctatetraenide or disodium ...
The lowest triplet state of an annulene is, according to Baird's rule, aromatic when it has 4n π-electrons and antiaromatic when the π-electron count is 4n + 2, where n is any positive integer. This trend is opposite to that predicted by Hückel's rule for the ground state , which is usually the lowest singlet state (S 0 ).
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Cyclooctatetraene (C 8 H 8) with eight π electrons has a nonplanar "tub" structure. However, the dianion C 8 H 2– 8 (cyclooctatetraenide anion), with ten π electrons obeys the 4n + 2 rule for n = 2 and is planar, while the 1,4-dimethyl derivative of the dication, with six π electrons, is also believed to be planar and aromatic. [8]